Look who's doling out dating advice now!

The state of Kelly Henderson's love life has been subject to lots of third-party opinions lately. But the tables have turned in this slightly awkward clip from Sunday's new Very Cavallari, which finds the stylist trying to make the best of an increasingly uncomfortable client appointment.

The "client" in question is Bobby Bones, a Nashville-based radio personality who has some history with Kelly.

"We were kind of loosely dating. And we have this amazing chemistry and connection and we still do," Kristin Cavallari's BFF tells the camera, while footage of Kelly helping Bobby disrobe—and re-robe again—before a photo shoot rolls across the screen. "But once we decided to start working together…it's always been a big thing for me, I'm not gonna date a client."

Bobby seems like he could be a little bit more flexible on that front. Minutes into their fitting and he's already asking her how things are going "with the dudes," before inexplicably offering to be a "consultant" for Kelly's potential suitors.

"What would you say?" she asks.

"‘Don't be alarmed by all the self-help audio all the time,'" he laughs, adding, "'There's a reason that we're in our mid 30s and we don't have anyone.'"

Though Kelly kindly tells Bobby to "speak for yourself, man," the aspiring romance adviser keeps going: "You just have to look at our histories," he continues. "We've had many, many relationships. They haven't worked. So we can plan on many, many more that don't as well."

Summoning all the pep talk prowess of her self-appointed former dating coach Jay Cutler, Kelly nips this pity party in the bud right away.  

"That's a very negative attitude," she smiles. "You should probably listen to one of the self-help tapes I have."

See their banter play out in the clip above! 

Brand new Very Cavallari every Sunday at 10 pm only on E!

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